Deuterated DMSO

Last updated
Deuterated DMSO
Wireframe of deuterated DMSO DMSO deuterated structure.png
Wireframe of deuterated DMSO
DMSO-d6.jpg
Names
Preferred IUPAC name
[(2H3)Methanesulfinyl](2H3)methane
Other names
Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
3D model (JSmol)
AbbreviationsDMSO-d6
1237248
ChemSpider
ECHA InfoCard 100.016.925 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-617-0
PubChem CID
RTECS number
  • PV6210000
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 Yes check.svgY
    Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N Yes check.svgY
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3
    Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3
    Key: IAZDPXIOMUYVGZ-WFGJKAKNEE
  • [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H]
Properties
C2D6OS
Molar mass 84.17 g/mol
Density 1.19 g/cm3 (20 °C)
Melting point 20.2 °C (68.4 °F; 293.3 K)
Boiling point 189 °C (372 °F; 462 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH3)2S=O)) with chemical formula ((CD3)2S=O) in which the hydrogen atoms ("H") are replaced with their deuterium ("D") isotope. Deuterated DMSO is a common solvent used in nuclear magnetic resonance spectroscopy (NMR).

Contents

Production

Deuterated DMSO is produced by heating DMSO in heavy water (D2O) with a basic catalyst such as calcium oxide. The reaction does not give complete conversion to the d6 product, and the water produced must be removed and replaced with D2O several times to drive the equilibrium to the fully deuterated product. [1]

Applications

NMR spectroscopy

C NMR Spectrum of DMSO-d6 13CNMR Spectra of DMSO d6.gif
C NMR Spectrum of DMSO-d6

DMSO is a good solvent for many organic compounds. Because deuterated DMSO does not contain any 1</1H atoms, it produces no peaks in 1H-NMR and as a result is commonly used as a solvent for NMR experiments. [2] Commercially available deuteriated DMSO is not isotopically pure. The residual DMSO-d5 produces a 1H-NMR signal observed at 2.50 ppm, which appears as a quintet (JHD=1.9Hz). In 13C-NMR, the chemical shift of DMSO-d6 is 39.52 ppm, and appears as a septet. [3]

Trideuteromethyl donor

Deuterated DMSO is used as a reagent for the introduction of a trideuteromethyl group (CD3) onto organic structures. [4]

References

  1. ↑ DEapplication 1171422B,Fruhstorfer, Wolfgang&Hampel, Bruno,"Process for the production of hexadeuterodimethyl sulfoxide",published 1964-06-04, assigned to E. Merck A.G.
  2. ↑ Chandak, MS; Nakamura, T; Takenaka, T; Chaudhuri, TK; Yagi-Utsumi, M; Chen, J; Kuwajima, K (22 January 2013). "The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments". Protein Sci . 22 (4). Hoboken, New Jersey, USA: Wiley-Blackwell: 486–91. doi:10.1002/pro.2221. PMC   3610054 . PMID   23339068.
  3. ↑ Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities". The Journal of Organic Chemistry . 62 (21). Washington, D.C., USA: American Chemical Society: 7512–7515. doi:10.1021/jo971176v. PMID   11671879.
  4. ↑ Steverlynck, Joost; Sitdikov, Ruzal; Rueping, Magnus (2021). "The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents". Chemistry – A European Journal. 27 (46): 11751–11772. doi:10.1002/chem.202101179. PMC   8457246 . PMID   34076925.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.